San Gimignano

One of the most charming and picturesque of all the Tuscan hill towns (and that’s saying a lot), San Gimignano is noted mainly for its medieval towers. They dominate the town in the way that skyscrapers dominate modern cities. At one time there were more than 70 towers (built as symbols of wealth and as a security precaution by the town’s prosperous merchants), but only 14 remain today. Walk through the wonderfully preserved town square, the Piazza della Cisterna, and visit the 13th-century town hall, the Palazzo del Popolo. There are good views from the Rocca citadel, and the entire town is a great place to stroll and soak up the atmosphere. If you visit on the third weekend in June, you’ll be rewarded with the Ferie dell Messi, a medieval parade in full costume followed by jousting tournaments. It takes quite a bit of time to get to San Gimignano from either Rome or Florence, so we suggest that you spend at least one full day and night there. That way, you’ll also get to see the town after the day-tripping tourist hordes have left. Another option is to stay in nearby Volterra, with its Etruscan ruins and vertiginous views from high on a forbidding hilltop. 25 mi/40 km southwest of Florence.